Methanol → 1-[3-Fluoro-4-(2,2,2-trifluoroacetyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 2383953

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:24]=3[CH3:25])[C:15]2=[O:26])[CH:5]=[CH:6][C:7]=1[CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10].CO>C(Cl)Cl.O=[Mn]=O>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:24]=3[CH3:25])[C:15]2=[O:26])[CH:5]=[CH:6][C:7]=1[C:8](=[O:13])[C:9]([F:12])([F:10])[F:11]

Participants

Conditions

Temperature: 50 °C

Procedure

MnO2 (536 mg, 6.165 mmol) was added to 1-[3-fluoro-4-(2,2,2-trifluoro-1-hydroxy-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-197a: 325 mg, 0.880 mmol) in DCM (20 mL) under nitrogen atmosphere. The resulting suspension was stirred at 50° C. overnight. The reaction was monitored by TLC (5% MeOH in DCM). The reaction mixture was cooled to room temperature and filtered through celite pad. The filtrate was washed with CHCl3, dried over Na2SO4 and concentrated. The concentrate was washed with hexane and dried to afford 240 mg of the product (74.53% yield).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through celite pad
washThe filtrate was washed with CHCl3
dry with materialdried over Na2SO4
concentrationconcentrated
washThe concentrate was washed with hexane
customdried

Sources & evidence

ORD record: ord-ee4cf1edb9684516b09950ee39a97b67
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263635B2

Linked notes

Loading…